반응 #487383

반응 방정식

7-oxabicyclo[4.1.0]heptane

sodium hydroxide

dibutylamine

triethyl-aluminium

→

trans-2-(N,N-dibutylamino)-cyclohexanol

수율 76.9%

용매

dichloromethane

hexane

반응 조건

후처리

1. 1
   기타the resultant reaction mixture
2. 2
   workup.STIRRINGstirred overnight
3. 3
   workup.STIRRINGthe mixture was stirred for 2 hours at room temperature
4. 4
   기타The phases were separated
5. 5
   세척the organic one was washed with water (2×50 ml)
6. 6
   기타over sodium sulfate and evaporated
7. 7
   workup.DISTILLATIONThe resultant crude was distilled under vacuum

실험 절차

A! A solution of 43 ml (0.25 mole) of dibutylamine in 770 ml of dichloromethane was added with a 0.91M solution of 280 ml (0.025 mole) of triethyl-aluminium in hexane, at 0° C. under argo, and the resultant reaction mixture was stirred for 30 minutes at room temperature, then dropwise added with 25.8 ml (0.25 mole) of 7-oxabicyclo[4.1.0]heptane, and stirred overnight. A 6M solution of 200 ml (1.2 moles) of sodium hydroxide was added very slowly, and the mixture was stirred for 2 hours at room temperature. The phases were separated, and the organic one was washed with water (2×50 ml), anhydrified over sodium sulfate and evaporated. The resultant crude was distilled under vacuum to provide 43.7 g (yield: 75%) of trans-2-(N,N-dibutylamino)-cyclohexanol (b.p.--105°-107° C./1 mmHg).

출처